Ossining Holidays from AU$3,258

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Your Ossining Holiday

With one of our holiday packages to Ossining, you'll find countless opportunities for fun and relaxation. There's tons to experience, including its rich history and spectacular views. Make your trip to Ossining even more fun by going sightseeing. Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall are among the popular attractions worth exploring. Don't delay your visit to this city any longer. Your ultimate Ossining holiday is only a few clicks away with Expedia.

The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Price was AU$4,272, price is now AU$3,258 per person
AU$3,258
per person
13 Nov - 20 Nov
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
8.6/10 Excellent! (20 reviews)
Small room but very clean

Reviewed on 13 Aug. 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Price was AU$4,511, price is now AU$3,325 per person
AU$3,325
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
7.6/10 Good! (870 reviews)
BEST – The hotel is very close to the Flatiron, with several subway lines reachable within a 5-minute walk. It’s clean, and the room is fine if you just need a place to shower and sleep. The front desk is available 24/7. WORST – Unfortunately, our room (707) was right next to a technical room, so we could hear mechanical noises day and night. We also asked for the TV to be fixed, but it was never taken care of.

Reviewed on 26 Aug. 2025

The Gallivant Times Square

The Gallivant Times Square

3.5 out of 5
Manhattan
Price was AU$4,583, price is now AU$3,507 per person
AU$3,507
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
6.4/10 (801 reviews)
Staff is friendly, helpful and accommodating. If you’re looking for a lux room to spend time in, this is not your place, but it is absolutely nice enough for someone who wants a comfortable, small, simple room to sleep in and have a private bathroom. Met all of our needs. Is clean. Bed is super comfortable. Clean HOT shower. On checkout day we extended our stay 2 extra days. Would def stay here again

Reviewed on 26 Aug. 2025

Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Manhattan
Price was AU$4,603, price is now AU$3,613 per person
AU$3,613
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8/10 Very Good! (2,075 reviews)
Super close to eberything. Great price and breakfast was good too. But lines are way too long in the morning and wish there were more elevators

Reviewed on 27 Aug. 2025

Holiday Inn NYC - Lower East Side by IHG

Holiday Inn NYC - Lower East Side by IHG

4 out of 5
Manhattan
Price was AU$4,690, price is now AU$3,695 per person
AU$3,695
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8.6/10 Excellent! (1,007 reviews)
Very friendly and clean

Reviewed on 23 Aug. 2025

Ossining Holiday

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre

Our pick of the best Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is AU$375 per night from 28 Aug to 29 Aug
AU$375
28 Aug - 29 Aug
includes taxes & fees
8.2/10 Very Good! (9 reviews)
"Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again."

Reviewed on 12 Aug. 2025

Windrose On Hudson
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 7 Sept to 8 Sept
AU$241
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,129 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."

Reviewed on 22 Aug. 2025

Hampton Inn White Plains/Tarrytown
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 1 Sept to 2 Sept
AU$197
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (2,219 reviews)
"Great location, very clean"

Reviewed on 24 Aug. 2025

Royal Regency Hotel
See all 1,214 properties in Ossining
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
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Discover the most popular places to visit in Ossining

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from AU$3,258 on Expedia. However, how much your holiday to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you're hoping to keep costs down. Another tip for scoring cheap Ossining holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodation, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Ossining. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.